Wingdale, NY Homes

• 

  $215,000 Sold Nov 20, 2025

  140 Dove Dr, Dover Plains, NY 12522

  • 2 Beds
  • 2 Baths
  • 1,680 Sq Ft
  • Built 2005

  Last Sold Summary

  • $128/SF
  • 41 Days On Market

  Last Listing Agent Richard Rennia Richard A. Rennia

  140 Dove Dr, Dover Plains, NY 12522
• 

  Est $557,626 Not Listed For Sale

  32 Meadow Brook Ln, Wingdale, NY 12594

  • 3 Beds
  • 2.5 Baths
  • 2,350 Sq Ft
  • Built 2003

  32 Meadow Brook Ln, Wingdale, NY 12594

  Last Sold Summary

  • 3% Above List Price
  • $230/SF
  • 29 Days On Market

  Last Sold Price $540,000

  Last Listing Agent Shannon Tully McGrath Realty Inc
• 

  

  

  /50

  $1,399,999

  • 6 Beds
  • 4.5 Baths
  • 4,200 Sq Ft

  57 Cedar Berry Ln, Dover Plains, NY 12522

  Just 90 miles from New York City, at the end of a winding, tree-lined drive, a world unfolds where time slows down, and life takes on a different rhythm. This is the Hudson Valley escape you’ve been waiting for. A custom-built home with detached workshop on nearly five private acres, where every detail was designed to bring comfort, inspiration, and beauty into daily living. The moment you

  Lindsay Stevens eXp Realty

  57 Cedar Berry Ln, Dover Plains, NY 12522
• 

  $1,750,000 Sold Oct 06, 2025

  783 N Clove Rd, Millbrook, NY 12545

  • 3 Beds
  • 3 Baths
  • 3,000 Sq Ft
  • Built 1986

  Last Sold Summary

  • 5% Below List Price
  • $583/SF
  • 33 Days On Market

  Current Estimated Value $1,795,193

  Last Listing Agent Dan Kessler Compass Greater NY, LLC

  783 N Clove Rd, Millbrook, NY 12545
• 

  Est $480,224 Not Listed For Sale

  29 Holly Hill Dr, Wingdale, NY 12594

  • 5 Beds
  • 3 Baths
  • 2,180 Sq Ft
  • Built 1996

  29 Holly Hill Dr, Wingdale, NY 12594

  Last Sold Summary

  • 32% Above List Price
  • $167/SF
  • 269 Days On Market

  Last Sold Price $365,000

  Last Listing Agent Brianna Bartlett eXp Realty
• 

  

  /22

  $389,000

  • 5 Beds
  • 2 Baths
  • 1,272 Sq Ft

  14 Dover Furnace Rd, Dover Plains, NY 12522

  Charming Five-Bedroom Home for Sale – 14 Dover Furnace Road, Dover Plains Welcome to this cozy five-bedroom, two-bath home featuring a spacious garage and a generously sized yard, perfect for outdoor enjoyment. The property has been thoughtfully updated with new gutters, new siding, central air conditioning, and a new propane boiler. Many repairs and improvements have already been completed,

  James Garcia Coldwell Banker Realty

  14 Dover Furnace Rd, Dover Plains, NY 12522
• 

  $35,000 Sold Jan 29, 2026

  9 Whatley Ln, Dover Plains, NY 12522

  • 3 Beds
  • 1 Bath
  • 864 Sq Ft
  • Built 1974

  Last Sold Summary

  • 6% Below List Price
  • $41/SF
  • 9 Days On Market

  Last Listing Agent Jamarr Zellner REALHome Services & Solutions

  9 Whatley Ln, Dover Plains, NY 12522
• 

  Est $464,352 Not Listed For Sale

  8 Hemlock Ln, Wingdale, NY 12594

  • 4 Beds
  • 3 Baths
  • 2,084 Sq Ft
  • Built 1995

  8 Hemlock Ln, Wingdale, NY 12594

  Last Sold Summary

  • 8% Above List Price
  • $206/SF
  • 54 Days On Market

  Last Sold Price $430,000

  Last Listing Agent Ryan Sylvestri RE/MAX
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  /11

  $175,000

  • 3 Beds
  • 1 Bath
  • 1,092 Sq Ft

  14 SE Mountain Rd, Wingdale, NY 12594

  RARE FIND !! FULLY DETACTED 3 BR / 1 BTH / SPLIT LEVEL SINGLE FAMILY HOUSE W UNFIN. BSMT & FULL REAR DECK W LARGE WRAP AROUND BACK YARD LOCATED IN THE HEART OF PEACE AND TRANQILITY OF WINGDALE.. Featurning 3 BR's + WALK IN LARGE PANTRY ( 1st Floor Walk In Bedroom) Living Room, Kitchen, Basement, Large Back & Side Yard. Septic Tank for plumbing and Underground Oil Tank For Heating (SELLER NOT

  Crystal Jones Voro LLC

  14 SE Mountain Rd, Wingdale, NY 12594
• 

  $409,000 Sold Sep 15, 2025

  198 Benson Hill Rd, Dover Plains, NY 12522

  • 4 Beds
  • 2 Baths
  • 1,656 Sq Ft
  • Built 1987

  Last Sold Summary

  • 5% Below List Price
  • $247/SF
  • 62 Days On Market

  Current Estimated Value $423,558

  Last Listing Agent LUCIANA BENNETT McGrath Realty Inc

  198 Benson Hill Rd, Dover Plains, NY 12522
• 

  Est $354,912 Not Listed For Sale

  27 Sycamore Blvd, Wingdale, NY 12594

  • 3 Beds
  • 1 Bath
  • 1,036 Sq Ft
  • Built 1994

  27 Sycamore Blvd, Wingdale, NY 12594

  Last Sold Summary

  • 6% Above List Price
  • $324/SF
  • 22 Days On Market

  Last Sold Price $336,000

  Last Listing Agent Vivian Morales Howard Hanna Rand Realty
• 

  /2

  $97,000

  • Land
  • 3.3 Acres
  • $29,394 per Acre

  488 Pleasant Ridge Rd, Poughquag, NY 12570

  Beautiful 3+ acres wooded lot in the Town of Union Vale. Convenient to TSP, Route 55 and Hudson River. BOHA.

  Graziano Tassone Tassone Realty Corp.

  488 Pleasant Ridge Rd, Poughquag, NY 12570
• 

  $805,000 Sold Jun 13, 2025

  0 Chestnut Ridge Rd Unit KEY823877, Dover, NY 12522

  • Land
  • 84.67 Acres
  • $9,507 per Acre

  Last Sold Summary

  • 1% Below List Price
  • 82 Days On Market

  Last Listing Agent Marie-Laure Collins Compass Greater NY, LLC

  0 Chestnut Ridge Rd Unit KEY823877, Dover, NY 12522
• 

  Est $346,835 Not Listed For Sale

  3677 Pleasant Ridge Rd, Wingdale, NY 12594

  • 3 Beds
  • 1 Bath
  • 1,632 Sq Ft
  • Built 1957

  3677 Pleasant Ridge Rd, Wingdale, NY 12594

  Last Sold Summary

  • 31% Above List Price
  • $162/SF
  • 65 Days On Market

  Last Sold Price $265,000

  Last Listing Agent Claudia Jiskra McGrath Realty Inc
• 

  

  /44

  $2,475,000

  • 4 Beds
  • 4.5 Baths
  • 2,412 Sq Ft

  56 Northrup Rd, Dover Plains, NY 12522

  At the very end of a quiet country road, you'll find 56 Northrup — a stunning, architect-designed retreat blending 19th-century farmhouse charm with thoughtful, award-winning modern design. Originally built in 1870 and reimagined by NYC architects Neumann & Rudy, this 33-acre property includes a restored main house, a sleek single-story primary suite addition, and expansive grounds featuring a

  Adam Hade Compass Greater NY, LLC

  56 Northrup Rd, Dover Plains, NY 12522
• 

  $205,000 Sold Jun 05, 2025

  126 Reagans Mill Rd, Wingdale, NY 12594

  • 2 Beds
  • 2 Baths
  • 1,048 Sq Ft
  • Built 1992

  Last Sold Summary

  • 15% Above List Price
  • $196/SF
  • 68 Days On Market

  Last Listing Agent Mark Snyder eXp Realty

  126 Reagans Mill Rd, Wingdale, NY 12594
• 

  Est $562,189 Not Listed For Sale

  15 Mountain Laurel Blvd, Wingdale, NY 12594

  • 3 Beds
  • 3.5 Baths
  • 2,742 Sq Ft
  • Built 1999

  15 Mountain Laurel Blvd, Wingdale, NY 12594

  Last Sold Summary

  • 12% Above List Price
  • $182/SF
  • 21 Days On Market

  Last Sold Price $500,000

  Last Listing Agent Jack Yao Realmart Realty LLC
• 

  $1,300,000 Sold Jul 31, 2025

  175 Kent Rd, Kent, CT 06757

  • 5 Beds
  • 4.5 Baths
  • 3,544 Sq Ft
  • Built 2002

  Last Sold Summary

  • $367/SF
  • 156 Days On Market

  Current Estimated Value $1,356,686

  Last Listing Agent John Engel Douglas Elliman of Connecticut

  175 Kent Rd, Kent, CT 06757
• 

  Est $405,010 Not Listed For Sale

  59 Holly Hill Dr, Wingdale, NY 12594

  • 3 Beds
  • 1.5 Baths
  • 1,640 Sq Ft
  • Built 1995

  59 Holly Hill Dr, Wingdale, NY 12594

  Last Sold Summary

  • 5% Above List Price
  • $235/SF
  • 36 Days On Market

  Last Sold Price $385,000

  Last Listing Agent Gillian Stewart Gillian Stewart Real Estate
• 

  $391,680 Sold May 27, 2025

  118 Lime Kiln Rd, Dover Plains, NY 12522

  • 3 Beds
  • 1.5 Baths
  • 1,524 Sq Ft
  • Built 1950

  Last Sold Summary

  • 2% Above List Price
  • $257/SF
  • 23 Days On Market

  Current Estimated Value $397,827

  Last Listing Agent Robin Bermudez Compass Greater NY, LLC

  118 Lime Kiln Rd, Dover Plains, NY 12522
• 

  Est $397,714 Not Listed For Sale

  115 Reagans Mill Rd, Wingdale, NY 12594

  • 3 Beds
  • 1.5 Baths
  • 1,380 Sq Ft
  • Built 1954

  115 Reagans Mill Rd, Wingdale, NY 12594

  Last Sold Summary

  • 20% Above List Price
  • $240/SF
  • 38 Days On Market

  Last Sold Price $331,000

  Last Listing Agent Claudia Jiskra McGrath Realty Inc
• 

  $350,000 Sold Nov 17, 2025

  593 Old State Route 22, Dover Plains, NY 12522

  • 2 Beds
  • 2 Baths
  • 1,144 Sq Ft
  • Built 1960

  Last Sold Summary

  • 22% Below List Price
  • $306/SF
  • 161 Days On Market

  Current Estimated Value $355,689

  Last Listing Agent Maureen McElduff Mullaney BHHS Hudson Valley Properties

  593 Old State Route 22, Dover Plains, NY 12522
• 

  Est $441,571 Not Listed For Sale

  16 Lilac Dr, Wingdale, NY 12594

  • 3 Beds
  • 3 Baths
  • 1,812 Sq Ft
  • Built 1997

  16 Lilac Dr, Wingdale, NY 12594

  Last Sold Summary

  • 10% Above List Price
  • $221/SF
  • 13 Days On Market

  Last Sold Price $400,000

  Last Listing Agent Iris Kalt Berkshire Hathaway Home Services
• 

  $465,000 Sold Sep 03, 2025

  18 Johnson Rd, Wingdale, NY 12594

  • 3 Beds
  • 2.5 Baths
  • 1,664 Sq Ft
  • Built 2003

  Last Sold Summary

  • $279/SF
  • 20 Days On Market

  Current Estimated Value $467,926

  Last Listing Agent Karen Gundelach Keller Williams NY Realty

  18 Johnson Rd, Wingdale, NY 12594
• 

  Est $419,267 Not Listed For Sale

  11 Holly Hill Dr, Wingdale, NY 12594

  • 3 Beds
  • 1.5 Baths
  • 2,269 Sq Ft
  • Built 1994

  11 Holly Hill Dr, Wingdale, NY 12594

  Last Sold Summary

  • 5% Above List Price
  • $176/SF
  • 156 Days On Market

  Last Sold Price $400,000

  Last Listing Agent Judith 'Judy' Albert BHHS Hudson Valley Properties
• 

  $1,036,000 Sold Jan 07, 2026

  Northrup Northrup Rd, Dover, NY 12522

  • Land
  • 86 Acres
  • $12,047 per Acre

  Last Sold Summary

  • 4% Below List Price
  • 238 Days On Market

  Last Listing Agent Robert D Ferris R. Ferris Real Estate, LLC

  Northrup Northrup Rd, Dover, NY 12522
• 

  Est $437,830 Not Listed For Sale

  4 Stone Pine Ln, Wingdale, NY 12594

  • 4 Beds
  • 2 Baths
  • 1,920 Sq Ft
  • Built 1993

  4 Stone Pine Ln, Wingdale, NY 12594

  Last Sold Summary

  • 3% Above List Price
  • $221/SF
  • 59 Days On Market

  Last Sold Price $425,000

  Last Listing Agent Kim Conklin KW MidHudson
• 

  $414,000 Sold Dec 31, 2025

  97 Lake Ellis Rd, Wingdale, NY 12594

  • 3 Beds
  • 2.5 Baths
  • 2,344 Sq Ft
  • Built 1950

  Last Sold Summary

  • 4% Above List Price
  • $177/SF
  • 63 Days On Market

  Current Estimated Value $417,059

  Last Listing Agent Amy Danis William Pitt Sotheby's Int'l

  97 Lake Ellis Rd, Wingdale, NY 12594
• 

  /2

  Est $359,807 Not Listed For Sale

  72 Reagans Mill Rd, Wingdale, NY 12594

  • 2 Beds
  • 1 Bath
  • 1,032 Sq Ft
  • Built 1962

  72 Reagans Mill Rd, Wingdale, NY 12594

  Last Sold Summary

  • 11% Below List Price
  • $315/SF

  Last Sold Price $325,000

  Last Listing Agent Joyce Brennan-Zolnik BHHS Hudson Valley Properties
• 

  $210,000 Sold May 06, 2025

  4 Pond View Ln, Sherman, CT 06784

  • Land
  • 2.17 Acres
  • $96,774 per Acre

  Last Sold Summary

  • 16% Below List Price
  • 94 Days On Market

  Current Estimated Value $215,301

  Last Listing Agent Barbara Sivba Coldwell Banker Realty

  4 Pond View Ln, Sherman, CT 06784
• 

  Est $430,899 Not Listed For Sale

  9 White Farm Rd, Wingdale, NY 12594

  • 3 Beds
  • 2 Baths
  • 1,554 Sq Ft
  • Built 1988

  9 White Farm Rd, Wingdale, NY 12594

  Last Sold Summary

  • 3% Above List Price
  • $270/SF
  • 47 Days On Market

  Last Sold Price $420,000

  Last Listing Agent Mark Boyland Keller Williams Realty Partner
• 

  $485,000 Sold Mar 31, 2026

  122 Susan Dr, Poughquag, NY 12570

  • 3 Beds
  • 2 Baths
  • 2,168 Sq Ft
  • Built 1985

  Last Sold Summary

  • 3% Below List Price
  • $224/SF
  • 236 Days On Market

  Current Estimated Value $495,329

  Last Listing Agent Susan Stevens BHHS Hudson Valley Properties

  122 Susan Dr, Poughquag, NY 12570
• 

  Est $414,349 Not Listed For Sale

  6 Millers Ln, Wingdale, NY 12594

  • 3 Beds
  • 2 Baths
  • 1,728 Sq Ft
  • Built 1989

  6 Millers Ln, Wingdale, NY 12594

  Last Sold Summary

  • 5% Above List Price
  • $229/SF
  • 46 Days On Market

  Last Sold Price $395,000

  Last Listing Agent Grace Vinciguerra RE/MAX
• 

  $512,500 Sold Feb 10, 2026

  28 Gobblers Knob Rd, Pawling, NY 12564

  • 3 Beds
  • 2 Baths
  • 2,107 Sq Ft
  • Built 1960

  Last Sold Summary

  • 32% Below List Price
  • $243/SF
  • 239 Days On Market

  Current Estimated Value $508,561

  Last Listing Agent Mark Snyder eXp Realty

  28 Gobblers Knob Rd, Pawling, NY 12564
• 

  Est $399,505 Not Listed For Sale

  4 Cross Way, Wingdale, NY 12594

  • 3 Beds
  • 1.5 Baths
  • 1,601 Sq Ft
  • Built 1989

  4 Cross Way, Wingdale, NY 12594

  Last Sold Summary

  • 14% Above List Price
  • $219/SF
  • 40 Days On Market

  Last Sold Price $350,000

  Last Listing Agent Nannette Fransen Houlihan Lawrence Inc.
• 

  $650,000 Sold Jul 17, 2025

  80-82 Connecticut 55, Sherman, CT 06784

  • 4 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • Built 1820

  Last Sold Summary

  • $325/SF
  • 30 Days On Market

  Last Listing Agent Irit Granger William Pitt Sotheby's Int'l

  80-82 Connecticut 55, Sherman, CT 06784
• 

  Est $409,676 Not Listed For Sale

  54 White Farm Rd, Wingdale, NY 12594

  • 3 Beds
  • 2 Baths
  • 1,539 Sq Ft
  • Built 2016

  54 White Farm Rd, Wingdale, NY 12594

  Last Sold Summary

  • 6% Above List Price
  • $250/SF
  • 107 Days On Market

  Last Sold Price $385,000

  Last Listing Agent Ishwar Rameshar YourHomeSold Guaranteed Realty
• 

  $1,150,000 Sold Apr 10, 2025

  8 River Oaks Ln, Sherman, CT 06784

  • 4 Beds
  • 5 Baths
  • 6,406 Sq Ft
  • Built 2006

  Last Sold Summary

  • $180/SF
  • 46 Days On Market

  Current Estimated Value $1,172,381

  Last Listing Agent Barbara Sivba Coldwell Banker Realty

  8 River Oaks Ln, Sherman, CT 06784
• 

  Est $348,523 Not Listed For Sale

  230 Dog Tail Corners Rd, Wingdale, NY 12594

  • 2 Beds
  • 2 Baths
  • 1,296 Sq Ft
  • Built 1941

  230 Dog Tail Corners Rd, Wingdale, NY 12594

  Last Sold Summary

  • 3% Above List Price
  • $262/SF
  • 58 Days On Market

  Last Sold Price $340,000

  Last Listing Agent Judith 'Judy' Albert BHHS Hudson Valley Properties
• 

  $1,200,000 Sold Jun 10, 2025

  206-208 Dog Tail Corners Rd, Wingdale, NY 12594

  • 6 Beds
  • 5 Baths
  • 5,532 Sq Ft
  • Built 2009

  Last Sold Summary

  • $217/SF
  • 37 Days On Market

  Last Listing Agent Ann Stettner Neil Charles Real Estate, LLC

  206-208 Dog Tail Corners Rd, Wingdale, NY 12594

Showing Results 121 - 160, Page 4 of 18